1,1'-Carbonyldiimidazole → HCID 58532566, compound

HRID 2069055Notes

Reaction equation

HRID 2069055 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C1N=CN([C:23](N2C=NC=C2)=[O:24])C=1.[NH2:30][C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34]([O:41][CH:42]([CH3:58])[CH2:43][C:44]2[CH:49]=[CH:48][N:47]=[C:46]([NH:50][C:51](=[O:57])[O:52][C:53]([CH3:56])([CH3:55])[CH3:54])[CH:45]=2)=[CH:33][CH:32]=1>C(Cl)Cl>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:23](=[O:24])[NH:30][C:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:34]([O:41][CH:42]([CH3:58])[CH2:43][C:44]3[CH:49]=[CH:48][N:47]=[C:46]([NH:50][C:51](=[O:57])[O:52][C:53]([CH3:54])([CH3:56])[CH3:55])[CH:45]=3)=[CH:33][CH:32]=2)[N:7]([C:11]2[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 682631,1'-Carbonyldiimidazole2×HCID 29741323-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-amine2×HCID 58532571HCID 58532571, compound

Product 1

HCID 58532566HCID 58532566, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent5×

Procedure

A solution of 3-tert-butyl-1-p-tolyl-1H-pyrazol-5-amine (5) (212 mg, 0.923 mmol) in DCM (1 mL) was added to a stirred solution of CDI (150 mg, 0.923 mmol) in DCM (1 mL), under nitrogen at RT over 5 min. After 1.5 hr a solution of tert-butyl 4-(2-(4-aminonaphthalen-1-yloxy)propyl)pyridin-2-ylcarbamate (49) (242 mg, 0.615 mmol) in DCM (2 mL) was added and stirring was continued at RT for 16 hr. A second portion of 3-tert-butyl-1-p-tolyl-1H-pyrazol-5-amine (141 mg, 0.615 mmol) in DCM (1 mL) was processed in a similar manner to the first, by reaction with CDI (100 mg, 0.615 mmol) in DCM (1 mL) and the resulting adduct was then added to the reaction mixture. After a further 2.5 hr the mixture was partitioned between water and DCM. The aqueous layer was extracted with DCM and the combined organic extracts were washed with brine and then dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 40 g, 0-100% EtOAc in isohexane, gradient elution) to afford the title compound (50) (163 mg, 40%) as a purple foam: m/z 649 (M+H)+ (ES+).

Workup

  1. additionthe resulting adduct was then added to the reaction mixture
  2. customAfter a further 2.5 hr the mixture was partitioned between water and DCM
  3. extractionThe aqueous layer was extracted with DCM
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by flash column chromatography (SiO2, 40 g, 0-100% EtOAc in isohexane, gradient elution)

Sources & evidence

ORD record
ord-7e9bb84c4cd3446f9606754a19d7549e
Source dataset
uspto-grants-2012_10
Patent number
US08299073B2

Reaction notes

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